Benzyl Bromide → HCID 66571683, compound

HRID 83678Notes

Reaction equation

HRID 83678 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]3[C:24](=[O:27])[NH:25][CH2:26][CH:20]3[CH2:19]2)=[O:17])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:32]([N:25]1[C:24](=[O:27])[CH:21]2[CH:20]([CH2:19][N:18]([C:16]([C:8]3[N:7]([CH2:6][C:5]4[CH:28]=[CH:29][C:2]([Cl:1])=[CH:3][CH:4]=4)[C:15]4[C:10]([CH:9]=3)=[CH:11][CH:12]=[CH:13][CH:14]=4)=[O:17])[CH2:23][CH2:22]2)[CH2:26]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 683797135-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)octahydro-1H-pyrrolo[3,4-c]pyridin-1-one

Product 1

HCID 66571683HCID 66571683, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)octahydro-1H-pyrrolo[3,4-c]pyridin-1-one (64 mg, 0.245 mmol) was dissolved in anhydrous DMF (5 mL). NaH (60% oil suspension, 29 mg, 0.735 mmol) was added at rt under nitrogen and stirred for 1 h. Benzylbromide (0.035 mL, 0.294 mmol) was added and stirring continued for 18 h under the same conditions. After this time, the solution was diluted with ethyl acetate and washed with 10% aq. sodium carbonate (2×), dried with magnesium sulfate, and concentrated in vacuo. Purification was done via silica gel flash chromatography (25 g silica, 80% EtOAc/hexanes.) The residue was dissolved in DCM, and rapid solvent removal afforded the title compound as a white powder. (Yield: 56 mg, 0.112 mmol, 72%) 1H NMR (400 MHz, CDCl3) 7.69, 7.33-6.99, 5.47, 4.56, 4.38, 4.11, 3.39-3.36, 2.94-2.82, 2.53-2.47, 1.75, 1.39

Workup

  1. stirringstirring
  2. waitcontinued for 18 h under the same conditions
  3. washwashed with 10% aq. sodium carbonate (2×)
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. dissolutionwas dissolved in DCM
  8. customrapid solvent removal

Sources & evidence

ORD record
ord-76b56644ceb4424499ef21bb57461d8b
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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